Chinese Journal of Organic Chemistry >
Synthesis of Iminopyrrolone Compounds
Received date: 2017-05-02
Revised date: 2017-06-16
Online published: 2017-06-23
Supported by
Project supported by the National Natural Science Foundation of China (Nos.21362042,21662042,U1202221,21262042),the Natural Science Foundation of Yunnan Province (No.2017FA003),the Talent Found in Yunnan Province (No.2012HB001),the Donglu Scholar of Yunnan University and the Excellent Young Talents in Yunnan University (No.XT412003).
The method was constructed for synthesis of pyrrolone compounds, which was based on the reaction of 1,1-endiamine (1) with maleic anhydride (2) in 1,4-dioxane at reflux in alkali condition (Et3N). As a result, a series of iminopyrrolone compounds have been synthesized by this reaction. This protocol possesses some advantages including readily available starting materials, simple operation and concise synthetic route and so on.
Key words： iminopyrrolone; nitro-enamine; synthesis
Zhao Yucheng , Xiao Qiang , Wang Baoqu , Lin Jun , Yan Shengjiao . Synthesis of Iminopyrrolone Compounds[J]. Chinese Journal of Organic Chemistry, 2017 , 37(10) : 2690 -2696 . DOI: 10.6023/cjoc201705004
[1] (a) Cramer, N.; Buchweiz, M.; Laschat, S.; Frey, W.; Baro, A.; Mathieu, D.; Richter, C.; Schwalbe, H. Chem.-Eur. J. 2006, 12, 2448.
(b) Cramer, N.; Laschat, S.; Baro, A.; Sehwalbe, H.; Richter, C. Angew. Chem., lnt. Ed. 2005, 44, 820.
(c) Yoshinari, T.; Ohmori, K.; Schrems, M. G.; Pfaltz, A.; Suzuki, K. Angew. Chem., lnt. Ed. 2009, 48, 1.
[2] Ondeyka, J.; Harris, G.; Zink, D.; Basilio, A.; Vicente, F.; Bills, G.; Collado, J.; Singh, S. B. J. Nat. Prod. 2009, 72, 136.
[3] (a) Lin, Z. J.; Lu, Z. Y.; Zhu, T. J.; Fang, Y. C.; Gu, Q. Q.; Zhu, W. M. Chem. Pharm. Bull. 2008, 56, 217.
(b) Sugie, Y.; Dekker, K. A.; Inagaki, T.; Kim, Y. J.; Sakakibara, J. A.; Kojima, Y. J. Antibiot. 2002, 55, 19.
(c) Heiiwig, V.; Grothe, T.; Bartschmid, A. M.; Endermann, R.; Geschke, F.; Henkei, T.; Stadler, M. J. Antibiot. 2002, 55, 881.
[4] (a) Wang, C. Y.; Wang, B. G.; Wiyowidagdo, S.; Wray, V.; Soest, R. V.; Steube, K. G.; Guan, H. S.; Proksch, P.; Ebel, R. J. Nat. Prod. 2003, 66, 51.
(b) Vangun, H. V. K.; Hertweck, C. Org. Biomol. Chem. 2007, 5, 1702.
(c) Vinale, F.; Flematti, G.; Sivasithamparam, K.; Lorito, M.; Marra, R.; Skelton, B.; Ghisalberti, E. L. J. Nat. Prod. 2009, 72, 2032.
(d) Li, j.; Liu, S.; Niu, S.; Zhuang, W.; Che, Y. J. Nat. Prod. 2009, 72, 2184.
[5] Regueiro-Ren, A.; Xue, Q.-M.; Swidorski, J. J.; Gong, Y.-F.; Mathew, M.; Parker, D. D.; Yang, Z.; Eggers, B.; D'Arienzo, C.; Sun, Y.-N.; Malinowski, J.; Gao, Q.; Wu, D.-D.; Langley, D. R.; Colonno, R. J.; Chien, C.; Grasela, D. M.; Zheng, M.; Lin, P.-F.; Meanwell, N. A.; Kadow, J. F. J. Med. Chem. 2013, 56, 1656.
[6] (a) Takeo, S.; Hayashi, H.; Miyake, K.; Takagi, K.; Tadokoro, M.; Takagi, N. Br. J. Pharmacol. 1997, 121, 477.
(b) Oyaizu, M.; Narahashi, T. Brain Res. 1999, 822, 72.
[7] (a) Royles, B. J. L. Chem. Rev. 1995, 95, 1981.
(b) Schobert, R.; Schlenk, A. Bioorg. Med. Chem. 2008, 16, 4203.
[8] Graupner, P.; Carr, A.; Clancy, E.; Gilbert, J.; Bailey, K. L.; Derby, J. A.; Gerwick, B. C. J. Nat. Prod. 2003, 66, 1558.
[9] Hardy, J.; Allsop, D. Trends Pharmacol. Sci. 1991, 12, 383.
[10] (a) Ramana, C. V.; Mondal, M. A.; Paranic, V. G.; Gurjar, M. K. Tetrahedron Lett. 2006, 47, 4061.
(b) Marquardt, U.; Schmid, D.; Jung, G. Synlett 2000, 1131.
[11] Zhuang, C.; Miao, Z.; Zhu, L.; Dong, G.; Guo, Z.; Wang, S.; Zhang, Y.; Wu, Y.; Yao, J.; Sheng C.; Zhang, W. J. Med. Chem. 2012, 22, 9630.
[12] Shorvon, S. Lancet 2001, 358, 1885.
[13] (a) Majumdar, P.; Pati, A.; Patra, M.; Behera, R. K.; Behera, A. K. Chem. Rev. 2014, 114, 2942.
(b) Eftekhari, B.; Zirak, M. Chem. Rev. 2015, 115, 151.
(c) Eftekhari, B.; Zirak, M.; Akbari, A. Chem. Rev. 2013, 113, 2958.
(d) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084.
(e) Wei, L.; Yang, X.; Yuan, J.; Hu, H.; Luo, G. Chin. J. Org. Chem. 2012, 32, 2339(in Chinese). (韦丽, 杨晓丽, 袁吉文, 胡宏纹, 陆国元, 有机化学, 2012, 32, 2339.)
(f) Tian, S.; Hao, Y. Chin. J. Org. Chem. 2013, 33, 2232(in Chinese). (田拴宝, 郝永兵, 有机化学, 2013, 33, 2232.)
[14] (a) Candeias, N. R.; Branco, L. C.; Gois, P. M. P.; Afonso, C. A. M.; Trindade, A. F. Chem. Rev. 2009, 109, 2703.
(b) Beutner, G. L.; Desai, L.; Fanfair, D.; Lobben, P. Anderson, E.; Leung, S. W.; Eastgate, M. D. Org. Process Res. Dev. 2014, 18, 1812.
(c) Xu, H.; Zhou, B.; Zhou, P.; Zhou, J.; Shen, Y.-H.; Yu, F.-C.; Lu, L.-L. Chem. Commun. 2016, 52, 8002.
(d) Grison, C.; Genève, S.; Coutrot, P. Tetrahedron Lett. 2001, 41, 3831.
(e) Kong, L.; Yang, R.; Du, X.; Yan, S.; Lin, J. Chin. J. Org. Chem. 2016, 36, 2437(in Chinese). (孔令斌, 杨瑞霞, 杜璇璇, 严胜骄, 林军, 有机化学, 2016, 36, 2437.)
[15] (a)Wang, M.-X.; Huang, Z.-T. J. Org. Chem. 1995, 60, 2807.
(b) Volodymyr, A. S.; Andriy, V. B.; Alexander, Y. P.; Mykhaylo, V. V. Synthesis 2007, 835.
[16] (a) Moya, A. D.; Macía, C. A.; García, T. M. I.; Vélez, C. H. Synth. Commun. 1996, 26, 1187.
(b) Luo, D.; Cui, S.; Hu, X.; Lin, J.; Yan, S. Chin. J. Org. Chem. 2017, 37, 166(in Chinese). (罗大云, 崔时胜, 胡兴梅, 林军, 严胜骄, 有机化学, 2017, 37, 166.)
[17] (a) Hubert, M.; Reinhard, T. Arch. Pharm. 1986, 319, 161.
(b) Hubert, M.; Reinhard, T. Arch. Pharm. 1987, 320, 1143.
[18] Jiang, X.-Y.; Liu, Z.-C.; Fang, L.; Yang, S.-J.; Lin, J. RSC Adv. 2014, 4, 26389.
[19] (a) Li, M.; Shao, P.; Wang, S.-W.; Kong, W.; Wen, L.-R. J. Org. Chem. 2012, 77, 8956.
(b) Yu, F.-C.; Huang, R.; Ni, X.-C.; Fan, J.; Yan, S.-J.; Lin, J. Green Chem. 2013, 15, 453.
(c) Yaqub, M.; Arif, N.; Perveen, R.; Batool1, J.; Riaz, M. T.; Yaseen, M. Asian J. Org. Chem. 2015, 27, 1013.
(d) Chen, X.-B.; Liu, Z.-C.; Lin, X.-R.; Huang, R.; Yan, S.-J.; Lin, J. ACS Sustainable Chem. Eng. 2014, 2, 2391.
(e) Chen, L.; Huang, R.; Du, X.-X.; Yan, S.-J.; Lin, J. ACS Sus-tainable Chem. Eng. 2017, 5, 1899.
(f) Yu, F.-C.; Lin, X.-R.; Liu, Z.-C.; Zhang, J.-H.; Liu, F.-F.; Wu, W.; Ma, Y.-L.; Qu, W.-W.; Yan, S.-J.; Lin, J. ACS Omega 2017, 2, 873.
(g) Peng, M.; Yang, R.; Liu, X.; Yan, S.; Lin, J. Chin. J. Org. Chem. 2015, 35, 1754(in Chinese). (彭美阳, 杨瑞霞, 刘昔敏, 严胜骄, 林军, 有机化学, 2015, 35, 1754.)
[20] (a) Yu, F.-C.; Yan, S.-J.; Hu, L.; Wang, Y.-C.; Lin, J. Org. Lett. 2011, 13, 4782.
(b) Yu, F.-C.; Hao, X.-P.; Lin, X.-R.; Yan, S.-J.; Lin, J. Tetrahedron 2015, 71, 4084.
(c) Li, M.; Zhou, Z.-M.; Wen, L.-R.; Qiu, Z.-X. J. Org. Chem. 2011, 76, 3054.
(d) Du, X.-X.; Huang, R.; Yang, C.-L.; Lin, J.; Yan, S.-J. RSC Adv. 2017, 7, 40067.
(e) Ma, Y.-L.; Wang, K.-M.; Huang, R.; Lin, J.; Yan, S.-J. Green Chem. 2017, 19, 3574.
(f) Cui, S.-S.; Huang, R.; Luo, D.-Y.; Yan, S.-J.; Lin, J. Eur. J. Org. Chem. 2017, 3442.
(g) Yang, R.; Zhao, Y.; Jiang, M.; Yan, S.; Lin, J. Chin. J. Org. Chem. 2016, 36, 2941(in Chinese). (杨瑞霞, 赵宇澄, 蒋美妤, 严胜骄, 林军, 有机化学, 2016, 36, 2941.)
(h) Chen, L.; Wang, B.; Zhao, Y.; Yan, S.; Lin, J. Chin. J. Org. Chem. 2017, 37, 1433(in Chinese). (陈亮, 王保取, 赵宇澄, 严胜骄, 林军, 有机化学, 2017, 37, 1433.)
[21] (a) Meziane, M. A.; Rahmouni, M.; Bazureau, J. P.; Hamelin, J. Synthesis 1998, 967.
(b) Dahmani, Z. M.; Rahmouni, R.; Brugidou, J. P.; Bazureau, J. Tetrahedron Lett. 1998, 39, 8453.
(c) Schafer, H.; Gruner, M.; Grobmann, G.; Gewald, K. Monatsh. Chem. 1991, 122, 959.
[22] Papmeyer, M.; Vuilleumier, C. A.; Pavan, G. M.; Zhurov, K. O.; Severin, K. Angew. Chem., Int. Ed. 2016, 55, 1685.
[23] Schirok, H.; Alonso-Alija, C.; Benet-Buchholz, J.; Goeller, A. H.; Grosser, R.; Michels, M.; Paulsen, H. J. Org. Chem. 2005, 70, 9463.
[24] (a) Kelly-Rowley, A. M.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 1995, 117, 3438.
(b) Kelly-Rowley, A. M.; Cabell, L. A.; Anslyn, E. V. J. Am. Chem. Soc. 1991, 113, 9687.
(c) Alizadeh, A.; Zarei, A.; Rezvanian, A. Synthesis 2011, 497.
[25] (a) Maryamabadi, A.; Hasaninejad, A.; Nowrouzi, N.; Mohbbi, G.; Asghari, B. Bioorg. Med. Chem. 2016, 24, 1408.
(b) Maryamabadi, A.; Hasaninejad, A.; Nowrouzi, N.; Mohebbi, G. Bioorg. Med. Chem. 2017, 25, 2507.
[26] Silva, R. C.; Silva, P. G.; Sangi, D. P.; Pontes, J. G.; Ferreira, A. G.; Corrêa, A. G.; Paixão, M. W. Tetrahedron 2013, 69, 9007.
[27] Liu, J.; Zhang, H.-R.; Lin, X.-R.; Yan, S.-J.; Lin, J. RSC. Adv. 2014, 4, 27582.
[28] Safron, S. A.; King, G. A.; Horvat, R. C. J. Am. Chem. Soc. 1981, 103, 6333.
[29] (a) Cassani, C.; Bergonzini, G.; Wallentin, C.-J. Org. Lett. 2014, 16, 4228.
(b) Tanner, D. D.; Osman, S. A. A. J. Org. Chem. 1987, 21, 4689.
/
| 〈 |
|
〉 |
